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3-(Morpholine-4-sulfonyl)benzohydrazide → 3-(4-Morpholinylsulfonyl)benzoic acid (2E)-2-[1-(3-chloro-2-fluorophenyl)ethylidene]hydrazide

HRID 877602
Notes
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Reaction equation

HRID 877602 reaction equation
[Cl:1][C:2]1[C:3]([F:11])=[C:4]([C:8](=O)[CH3:9])[CH:5]=[CH:6][CH:7]=1.[O:12]1[CH2:17][CH2:16][N:15]([S:18]([C:21]2[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=2)[C:24]([NH:26][NH2:27])=[O:25])(=[O:20])=[O:19])[CH2:14][CH2:13]1>CO.C(O)(=O)C>[Cl:1][C:2]1[C:3]([F:11])=[C:4](/[C:8](=[N:27]/[NH:26][C:24](=[O:25])[C:23]2[CH:28]=[CH:29][CH:30]=[C:21]([S:18]([N:15]3[CH2:16][CH2:17][O:12][CH2:13][CH2:14]3)(=[O:19])=[O:20])[CH:22]=2)/[CH3:9])[CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 8772463-(Morpholine-4-sulfonyl)benzohydrazideHCID 111165311-(3-Chloro-2-fluorophenyl)ethan-1-one

Product 1

HCID 727925513-(4-Morpholinylsulfonyl)benzoic acid (2E)-2-[1-(3-chloro-2-fluorophenyl)ethylidene]hydrazideYield 43.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887Methanol
Solvent

Conditions

Temperature
120 °C

Procedure

1-(3-Chloro-2-fluorophenyl)ethanone (20 mg, 0.116 mmol) and 3-(morpholinosulfonyl)benzohydrazide (33.1 mg, 0.116 mmol) were dissolved in methanol (4 mL) in the presence of acetic acid as a catalyst, and the reaction mixture was heated via microwave irradiation to 120° C. for 30 min. Following cooling, the solvent was removed by vacuum and the resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2) affording the title compound (22 mg) as a solid. 1H NMR (400 MHz, CDCl3): δ 9.43 (s, 1H), 8.37 (m, 1H), 8.16 (m, 1H), 7.87 (d, 1H, J=7.2 Hz), 7.65 (m, 1H), 7.41 (m, 1H), 7.10 (t, 1H, J=8.0 Hz), 3.71 (m, 4H), 2.95 (m, 4H), 2.38 (s, 3H). ESI-MS: 440.1 [M+H]+.

Workup

  1. temperatureFollowing cooling
  2. customthe solvent was removed by vacuum
  3. customthe resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-7ed1b0cb3f1547088b736a0b311047be
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08987335B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes